First Synthesis of Diindeno[1,2-g:1',2'-s]rubicene Derivatives and their Evaluation as Semiconductors

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Abstract

Solution-processable derivatives 4a–d of the novel diindeno[1,2-g:1',2'-s]rubicene ring system have been prepared in three steps from 1,5-dichloroanthraquinone. Charge extraction by linearly increasing voltage measurements indicates that 4a–d have bulk mobilities <10–7 cm2 V–1 s–1. Consistent with these low mobility values, field-effect transistors fabricated from 4a–d show poor performance. X-ray crystallographic analyses indicate that in the crystalline state, molecules of compounds 4b–d pack in a manner that hinders p–p stacking, thus preventing strong electronic coupling between molecules that is essential for high charge mobility semiconductor performance.

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